Iodine → HCID 69556632, compound

HRID 479154Notes

Reaction equation

HRID 479154 reaction equation
[CH2:1]([O:3][C:4](=[O:33])/[C:5](/[O:30][CH2:31][CH3:32])=[CH:6]/[C:7]1[C:12]([CH3:13])=[CH:11][C:10]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[O:20][C:21]=2[CH3:22])=[CH:9][C:8]=1[CH3:29])C.II.[Mg]>CO>[CH3:1][O:3][C:4](=[O:33])[CH:5]([O:30][CH2:31][CH3:32])[CH2:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([O:14][CH2:15][CH2:16][C:17]2[N:18]=[C:19]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[O:20][C:21]=2[CH3:22])=[CH:9][C:8]=1[CH3:29]

Participants

5

Reactant 3

HCID 807IodineHCID 5462224Magnesium2×HCID 69556202HCID 69556202, compound

Product 1

HCID 69556632HCID 69556632, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 30 mg of 3-{2,6-dimethyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2Z-ethoxy-acrylic acid ethyl ester in 1.5 ml of methanol was subsequently added 1 mg of iodine and 17 mg of magnesium and stirring was continued for 3 h. A further portion of 67 mg of magnesium was added and stirring was continued for 1.5 h. The suspension was filtered, the filtrate evaporated and the residue separated on prep. HPLC (RP-18, CH3CN/H2O, gradient) to give 2 mg (7%) of the title compound as a white solid.

Workup

  1. stirringstirring
  2. waitwas continued for 1.5 h
  3. filtrationThe suspension was filtered
  4. customthe filtrate evaporated
  5. customthe residue separated on prep

Sources & evidence

ORD record
ord-47620be2f83d4ed6ba955f1a0d8a588e
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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